Permanent finish for textiles



Patented Mar. 20, 1945 2,371,892 PERMANENT FINISH ron TEXTILES John M.Hood, Old Greenwich, Conn, assignor to American Cyanamid Company, NewYork, N. Y.,

a corporation of Maine No Drawing. Application August 30, 1941,

- Ser al No. 408,991

8 Claims.

A further object is the provision of a finish of this type that isresistant to soaping and laundering and which will therefore have a longeffective life after its application to the fabric.

I have discovered that the above and other desirable characteristics areexhibited by compositions comprising essentially mixtures of alkylateclr alcohol-reacted melamine-aldehyde condensation products and salts ofalkoxypropylamines. Textile treating compositions containing these twoessential classes of ingredients are readily applied to textile threadsand fibers in the form of aqueous emulsions and when properly cured theyare both water-repellent and durable in character.

The alkylated or alcohol-reacted melaminealdehyde condensation productsare resinous in character, and it has previously been proposed to applythem to textile fabrics for creaseproofing purposes. I have nowdiscovered that the resins of this class, when used in the form ofsolutions in organic solvents, can be emulsified or dispersed in waterby the addition of relatively small quantities of alkoxypropylaminesalts, and that the resulting aqueous emulsions or dispersions can beemployed as textile finishing baths. When textile fibers or fabrics suchas cotton, wool, viscose, vinyl polymer, cellulose acetate, spun rayonand the like are impregnated in such baths, dried and cured for a fewminutes at reasonably high temperatures they become hydrophobic incharacter and are resistant to both water and to stains carried by waterand alcohol.

Although a wide range of alkoxypropylamine salts may be used asemulsifying agents for alcohol-reactecl melamine-aldehyde resins such asbutylated melamine-formaldehyde resin, I have found that the molecularweight of the amine has an important bearing on the ultimateWater-repellent characteristics of the finished composition. Thus, forexample, a compound of relatively low molecular weight such asCH1i.O.C3HsNI-Iz, when used in the form of its acetate or other salt,produces a finish of relatively low water-repellency as compared withhigher homologs such as the octyloxypropylamine, decyloxypropylamine anddodecyloxypropylamine acetates or other 1 salts. Still betterwater-repellency is frequently obtained with salts of secondary ortertiary amines in whiph at least one of the two additional-substituentchains of the amine is also of relatively high molecular weight, and thebest waterproofing properties are exhibited by secondary or tertiaryalkoxypropylamine salts in which the amine contains at least twoalkoxypropyl groups of substantial molecular weight. From what has beensaid, it is evi-- dent that the water-resistant properties of V'Llouscompositions falling witihin the scope of my invention will improvegradually with the number of carbon atoms in the amir 1 salts and it istherefore rather-difficult to assign-any definite lower limit ofoperative-ness. On the basis of numerous tests, however, it can bestated that the alkoxypropylamine salt should contain at least elevencarbon atoms, and in most cases it is preferable to have at least eightcarbon atoms in the alkyl radical forming the alkoxypropyl group of theamine. For better results it is usually advisable to employ analkoxypropylamine salt in which the alkyl radical contains from 12-18carbon atoms, and the, best results have been obtained withbis-octadecoxypropylamine salts.

Representative compounds that have given the most satisfactory resultsare bis(3-N-octadecoxypropyl) amine acetate, hydrochloride, sulfate,hydroxyisobutyrate, etc., and similar salts of 3-N-octadecoxypropylamine, bis(3 N dodecoxypropyl) amine, N-butyl-bis(3 Noctadecoxypropyl) amine, methyl bis(3 N octadecoxypropyl) amine, andbis(3-hexadecoxypropyl)amine.

The alkylated melamine-aldehyde resins with which the above compoundsare employed are known, and need not be discussed in great detail. It isknown that melamine can be condensed with formaldehyde, acetaldehyde,propionaldehyde, butyraldehyde, benzaldehyde and the like in. molarratios of 1:2 up to and including 1:6 to form resinous complexes. As isdescribed in greater detail in U. S. Patent No. 2,197,357 thesecomplexes can be transformed into organic solvent-soluble alkylated"compounds by further reaction with alcohols such as methyl, ethyl,propyl, butyl, amyl, hexyl, octyl or benzyl alcohols, preferably in thepresence of a small quantity of an acid condensation catalyst such asphosphoric acid. Preferably an excess of the alcohol is used and themixture is heated until substantially all the water has been removed,whereupon there is obtained a solution of the resinous material in theexcess solvent. The solution may then be fur- 3-N-octadecoxypropylamine.rnixed amine of theformula ther diluted with other alcohols or withlimited amounts of hydrocarbon solvents such as toluene. xylene and thelike.

In preparing the textile finishing compositions of the presentinvention, I find that the best resuits are obtained withmelamine-formaldehyde condensation products containing from 2-5 andpreferably about 4 moles of formaldehyde 1 or each mole of melamine,These condensation products are preferably reacted with lower aliphaticalcohols such methyl alcohol or butyl alcohol to the solvent-solublestage, after which amounts of other organic solvents may be added. Asuitable alkoxypropylamine salt is then preferably dissolved at roomtemperature in the resin solution whereupon water is slowly added withrapid, efficient stirring until an emulsion of the water-in-oil typehaving a particle size of one micron or less is obtained. Forapplication to the fabrics this emulsion is further diluted with about 5to times its weight of water at 70120 F. and the cloth is passed throughthe bath under .conditions such that the amount of finish will rangefrom 3% to 12%. The cloth is then preferably dried for about 5 minutesat 240-250 F. after which the resin is cured for 4 minutes at 285-310 F.or higher.

Cloth finished by the above process has a soft, full hand and good waterrepellency, which are characteristics that have been much desired in thetrade. Tests carried out at a number of commercial laundries have proventhe finish to have good resistance both to laundering and to drycleaning. The finish is compatible with corn starch, gelatin and locustbean gum, and the latter actually improves the hand of the treatedfabric when incorporated into the textile treating bath. The finish iscompletely stable upon storage and undesirable odors are not generatedeven upon storage in temperate climates.

The invention will be illustrated in greater detail by the followingspecific examples. It should be understood, however, that while theseexamples may describe in detail some of the more specific features ofthe invention, they are given primarily for illustrative purposes andthe invention in its broader aspects is not limited thereto.

Example I was also present.

21.2 parts by weight of the above product was melted and stirred at 83C. and 2.42 parts of glacial acetic acid were added. The stirring wascontinued until the salt formation was complete. after which the batchwas cooled.

12 parts by weight of the above mixture of amine salts were dissolved atroom temperature in '48 parts of a solution containing by weightsuitable I of the butyl alcohol reaction product ot-tetramethylolmelamine dissolved in a mixture of became a soft paste that could beeasily stirred.

The product is stable at both low and high temperatures. It has beenfrozen at the extremely low temperature of solid carbon dioxide withoutpermanent damage. Samples stored at 122 F. for 500 hours and at roomtemperatures for several months have been satisfactory for immediateuse. The pH of the emulsion as prepared may vary from 3.5 to 4.5, butcan be adjusted over a much wider range without affecting the stabilityof the emulsion.

A portion of the batch was diluted by stirring into 6 times its weightof water warmed to 70- F. and cloth was passed through the bath and thendried for 5 minutes at 240250 F. The cloth was then heated on tenterframes for 4 minutes at 285 F. to cure the finish. 80 x 80 bleachedcotton percale was finished in this manner and sent to a commerciallaundry for a regular laundering including high temperature F.) soaping,chlorine bleach, and rinsing and also a regular colored goods washconsisting of low temperature (120 F.) soaping and rinsing. Samples of68 x 60 spun rayon, 4.59 yards p r pound in weight, were also finishedwith 3% and 4.5% of the finish and sent to the same laundry for thecolored goods Wash only. The fabrics were then tested forwater-repellency by subjecting a weighed six-inch square to a. finespray of water at 70 F. for one minute and determine the increase inweight. The results were as follows:

Percent Water absorbed A finish similar to that described in Example 1was prepared, but an octyl alcohol-reacted pentamethylol melamine wassubstituted for the butylated compound. The emulsion was diluted withwater for application and bleached 80 x 80 cotton percale wasimpregnated and cured for six minutes at 290 F. After sea-ping for 1hour and 2 hours in 0.5% soap and 0.2% soda ash at 160 F. the clothretained 92% and 81%, respectively, of the finish. Spray tests similarto those described in Example 1 showed a percentage water absorption of50.3 for the original treated fabric, 54.0 for the fabric after one hoursoaping and 60.4 after 2 hours.

Example 3 Finishes similar to the composition of Example 1 were preparedin which 7, 8, 9, 10 and 11 parts of the amine salt were incorporatedinstead of the 12 parts previously described. It was found that the heatstability of the emulsion was lowered by this reduction.

Example 4 12 parts by weight of N-butyl bis(3-N-octadecoxypropyl) amineacetate were dissolved in 48 parts of a 50% solution of butylatedmelamineformaldehyde resin and the mixture was emulsified in water witheflicient high-speed stirring. The emulsion was diluted, applied tocloth, and dried and cured by heating in the usual manner.

The treated cloth was found to be equal in waterrepellent properties andas resistant to laundering as the product of Example 1, and possessedthe further advantage that there was no chlorine absorption duringbleaching in the laundry.

What I claim is:

1. A composition for finishing textiles which comprises essentially amixture of an alcohol-reacted melamine-aldehyde condensation product anda salt of an alkoxypropylamine containing at least eleven carbon atoms.

2. A composition for finishing textiles which comprises essentially amixture of an-alcohol-reacted melamine-aldehyde condensation product anda salt of an alkoxypropylamine corresponding to the formula 7 of the inwhich R is an alkyl radical containing at least eight carbon atoms, R1is a member of the group consisting of hydrogen and alkyl radicals and Xis a salt-forming anion.

5. A composition for finishing textiles which comprises essentially amixture of an alcohol-reacted melamine formaldehyde condensationproductand a salt of an octade'coxypropylamine corresponding to the formulaC|lHI'I"0.C3Hc N .k

in which R1 is a member of the groupconsisting of hydrogen'and alkylradicals, R2 is a, member group consisting of hydrogen and alkoxylradicals andxis a salt-forming anion.

in which R is an alkyl radical, R1 is a member of the group consistingof hydrogenand alkyl radi cals, R: is a member of the group consistingof hydrogen and alkoxyl radicals and X is a saltin which R is an alkylradical, R1 is a member of the group-consisting of hydrogen and alkylradicals, R: is a member of. the group consisting of hydrogen andalkoxyl radicals and X is a salt forming anion and in which a total ofat least in which lit: is amember' of the group consistingfipkcomposition for flnishing textiles which comprises essentially amixture of an alcoholreacted melamineformaldehyde vcondensation productand a salt of .anioctadecoxypropylamine corresponding to the formula ofhydrogen and alkyl radicals and X-is 81-58."? forming anion. 3

'7. A composition for finishing textiles hol-reactedmelamine-formaldehyde condensation product and a salt ofbls(3-N-octadecoxypropyl) amine.

a. A comments for finishing textiles which comprises essentially thebutyl alcohol reaction product of a melamine-formaldehyde condensationproduct containing about four molecules of formaldehyde for eachmolecule of'melamine together with a salt of bis(3-N-octadeco1wpropyl)amine.

' JOHN M. HOOD.

which 7 comprises essentiall a mixture of a .butylalco-

